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US4897355A
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N[ω,(ω-1)-dialkyloxy]- and N-[ω,(ω-1)-dialkenyloxy]-alk-1-yl-N,N,N-tetrasubstituted ammonium lipids and uses therefor
Assignee: Syntex USA LLC
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Filing: 1987-10-29
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Granted: 1990-01-30
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Expires: 2007-10-29
Abstract
Abstract This invention relates to compounds of the formula <IMAGE> I or an optical isomer thereof wherein R1 and R2 are the same or different and are an alkyl or alkenyl group of 6 to 24 carbon atoms; R3, R4 and R5 are the same or different and are alkyl of 1 to 8 carbon atoms, aryl, aralkyl of 7 to 11 carbon atoms, or when two or three of R3, R4, and R5 are taken together to form quinuclidino, piperidino, pyrrolidino, or morpholino; n is 1 to 8; and X is a pharmaceutically acceptable anion.
Inventors
- 👤 Deborah A. Eppstein
- 👤 Philip L. Felgner
- 👤 Thomas R. Gadek
- 👤 Gordon H. Jones
- 👤 Richard B. Roman
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 20:26
CPC Classifications
C; C07; C07D; C07D453/00; C07D453/02; A; A61; A61K; A61K9/00; A61K9/0012; A61K9/0014; A61K9/0019; A61K9/10; A61K9/127; A61K9/1271; A61K9/1272; C12; C12N; C12N15/00; C12N15/09; C12N15/87; C12N15/88; Y; Y10; Y10S; Y10S435/00; Y10S435/8215; Y10S435/822; Y10S435/829
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
139 words
A method for introducing a polyanion into a cell, said method comprising: forming a liposome from a positively charged lipid of Formula I ##STR8## or an optical isomer thereof wherein R 1 and R 2 are the same or different and are an alkyl or alkenyl group of 6 to 24 carbon atoms; R 3 , R 4 and R 5 are the same or different and are alkyl of 1 to 8 carbon atoms, aryl, aralkyl of 7 to 11 carbon atoms, or when two or three of R 3 , R 4 , and R 5 are taken together to form quinuclidino, pyrrolidino, piperidino, or morpholino; n is 1 to 8; and x is a pharmaceutically acceptable anion; contacting the liposome with a polyanion to form a positively-charged polyanion-liposome complex; and incubating the complex with a cell.
Claim 2
Independent Claim
139 words
A method for introducing a polyanion into a cell, said method comprising: forming a liposome from a positively charged lipid of Formula I ##STR8## or an optical isomer thereof wherein R 1 and R 2 are the same or different and are an alkyl or alkenyl group of 6 to 24 carbon atoms; R 3 , R 4 and R 5 are the same or different and are alkyl of 1 to 8 carbon atoms, aryl, aralkyl of 7 to 11 carbon atoms, or when two or three of R 3 , R 4 , and R 5 are taken together to form quinuclidino, pyrrolidino, piperidino, or morpholino; n is 1 to 8; and x is a pharmaceutically acceptable anion; contacting the liposome with a polyanion to form a positively-charged polyanion-liposome complex; and incubating the complex with a cell.
Claim 3
Dependent Claim
48 words
A method according to claim 1 wherein R 1 and R 2 are the same and are alkyl of 10 to 20 carbon atoms, R 3 , R 4 , and R 5 are methyl or ethyl, n is 1 to 4 and X is a halide ion.
Claim 4
Dependent Claim
10 words
A method according to claim 2 wherein n is 1.
Claim 5
Dependent Claim
20 words
The method of claim 3, wherein the compound of Formula I is (±) N-(2,3-di-(9-(Z)-octadecenyloxy))-prop-1-yl-N,N,N-trimethylammonium chloride or an optical isomer thereof.
Claim 6
Dependent Claim
11 words
The method of claim 1 wherein the polyanion is a polynucleotide.
Claim 7
Dependent Claim
11 words
The method of claim 1 wherein the polyanion is a polypeptide.
Claim 8
Dependent Claim
13 words
The method of claim 1 wherein the incubating step is done in vitro.
Claim 9
Dependent Claim
13 words
The method of claim 1 wherein the incubating step is done in vivo.
Claim 10
Dependent Claim
21 words
The method of claim 1 comprising the further step of administering the transfection transfected cell to a subject in need thereof.
Claim 11
Independent Claim
133 words
A method for introducing a biologically active substance into a cell, said method comprising: forming a liposome comprising: a compound of Formula I: ##STR9## or an optical isomer thereof wherein R 1 and R 2 are the same or different and are an alkyl or alkenyl group of 6 to 24 carbon atoms; R 3 , R 4 and R 5 are the same or different and are alkyl of 1 to 8 carbon atoms, aryl, aralkyl of 7 to 11 carbon atoms, or when two or three of R 3 , R 4 , and R 5 are taken together to form quinuclidino, pyrrolidino, piperidino, or morpholino; n is 1 to 8; and X is a pharmaceutically acceptable anion; and a biologically active substance; and incubating the liposome with a cell culture.
Claim 12
Independent Claim
133 words
A method for introducing a biologically active substance into a cell, said method comprising: forming a liposome comprising: a compound of Formula I: ##STR9## or an optical isomer thereof wherein R 1 and R 2 are the same or different and are an alkyl or alkenyl group of 6 to 24 carbon atoms; R 3 , R 4 and R 5 are the same or different and are alkyl of 1 to 8 carbon atoms, aryl, aralkyl of 7 to 11 carbon atoms, or when two or three of R 3 , R 4 , and R 5 are taken together to form quinuclidino, pyrrolidino, piperidino, or morpholino; n is 1 to 8; and X is a pharmaceutically acceptable anion; and a biologically active substance; and incubating the liposome with a cell culture.
Claim 13
Dependent Claim
48 words
A method according to claim 10 wherein R 1 and R 2 are the same and are alkyl of 10 to 20 carbon atoms, R 3 , R 4 , and R 5 are methyl or ethyl, n is 1 to 4 and x is a halide ion.
Claim 14
Dependent Claim
10 words
A method according to claim 11 wherein n is 1.
Claim 15
Dependent Claim
20 words
A method of claim 12, wherein the compound of Formula I is (±) N-(2,3-di-(9-(Z)-octadecenyloxy))-prop-1-yl-N,N,N-trimethylammonium chloride or an optical isomer thereof.
References Cited (Backward Citations)
EP0187702A1
Cited
EP0188311A2
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-01-29 | 1993-07-31 | 1994-01-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-01-29 | 1997-07-31 | 1998-01-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-01-29 | 2001-07-31 | 2002-01-30 | $7700.00 | Window Closed / Lapsed |